Reaction #44941

Reaction equation

2-methylaminoethanol

4-hydroxybenzylideneacetone

→

compound ( b )

benzylidene acetone

Solvents

NaHSO3

H2O

Conditions

Procedure

It should be noted that an initial reaction of 2-methylaminoethanol (1.5 mL) with 4-hydroxybenzylideneacetone (0.68 g) in NaHSO3 (0.78 g) and H2O (1.5 mL) in a sealed vial at 140° C. for 16 hrs did not provide the necessary benzylidene acetone derivative (Scheme 1, compound (b)). Therefore, N-methyl-N-(2-hydroxyethyl)-4-aminobenzaldehyde (Scheme 1, compound (a)) was purchased and used to complete the first step of synthesis instead. When the benzylidene acetone derivative was spotted on a TLC plate the compound glowed fluorescently. The benzylidene acetone derivative reaction mixture was spotted onto preparative TLC plate for purification. Three distinct bands can be observed: a red band at the bottom of the plate, yellow band at the middle, and a faint band at the top were observed. Using mass spectra the inventors determined that the middle yellow band contained the actual benzylidene acetone derivative.

Source